Tougher Than Leather: Willie Nelson Turns 90

Reflections on an American treasure

Willie Nelson on the cover of his 2021 Sinatra album That’s Life (Image: Legacy Recordings)

There are few pre-Boomer musical greats still with us, let alone ones who achieved success among fans of genres well beyond the artist’s own.

This may be Rock & Roll Globe, but Willie Nelson, who turns 90 today, is a country artist whose popularity has transcended that genre. A lot of folks back in the day had Willie mixed in with those Pink Floyd, Zeppelin, Beatles and Boston records.

He’s earned his place in pop culture, but he’s not a museum piece. He’s not just a legendary figure in music, but one who is still regularly putting out new material.

To state the glaringly obvious, Nelson has been at this a long time. His first album and first hit single were released when JFK was president. His first pop hit, when he was 42, was a cover of “Blue Eyes Crying In The Rain” that kept company with the likes of KC & The Sunshine Band, ABBA, the Bee Gees, KISS and, ahem, Morris Albert. I Don’t Know a Thing About Love, released in March, is his 73rd studio album (a number that goes up to 99 if you count collaboration albums).



Nelson’s remained adept at covering others’ material, with his most recent album (released last month) being a tribute to songwriter Harlan Howard, who gave Nelson one of his big breaks all those years ago. But he’s also been a damned fine writer himself. While working three jobs (radio disc jockey, musician, guitar instructor) at one time, none of which paid well, he wrote “Crazy”, “Night Life”, “Funny How Time Slips Away” and “Hello Walls”, all of which would become country standards, in about two weeks.

Still, it took some time. Nelson was working as an encyclopedia salesman in Nashville when he started being able to sell songs, with a big one happening when singer-songwriter Hank Cochran and producer Owen Bradley sold an initially reluctant Patsy Cline on recording “Crazy”, a song that Nelson had trouble selling because it had more than three chords.

Nelson waited in the car one day while Cochran made his pitch. Cochran told Andrew Dansby of the Houston Chronicle, “Patsy asked, ‘Does he think he’s too good to come into my session? I said, ‘He probably does, why don’t you go out there and kick his ass?’”

Nelson came in, no ass kicking required, and Cline agreed to do the song, eventually putting her own spin while retaining the core of Nelson’s arrangement. The song became a massive country hit, a Top 10 pop single and the song she’d be most associated with in her tragically short career.


VIDEO: Willie Nelson performs “Crazy” at Austin City Limits in 2018

His success as a songwriter opened the door for Nelson to finally get to record albums, just as they were starting to become more widespread after the business had been geared so much towards singles.

Starting with his 1962 debut …And Then I Wrote, Nelson would release nine albums over the rest of the decade. Three of those would reach the Top 10 of the country charts, with nine Top 40 country singles over that span.

Nelson was frustrated. He was often put into the label-induced constraints of the time, forced production choices in efforts to “find a hit” often with little time to work out material with others in the studio.

As the ’70s began, Nelson started to branch out. On 1970’s Both Sides Now, he covered Joni Mitchell and Fred Neil. 

He also started to feel less at home in the short hair and suit-and-tie look, as he identified less with conformist conservative Nashville of the period and more with the counterculture.  In his 2015 autobiography It’s A Long Story: My Life with David Ritz, Nelson said, “I liked that they put flowers in their hair and wore bright tie-dyed blouses and bell-bottomed pants. I liked that they had the courage to look and act any damn way they pleased.”

Things weren’t going well. Nelson and his first wife divorced. His Tennessee ranch had burned down. His songwriting royalties were often eaten up by the cost of touring. RCA Records’ efforts to make Wilson a star, often by trying to put a square peg into a round hole, clashed with his songwriting instincts. Chet Atkins, in what proved to not be one of his better decisions, wouldn’t let Nelson record with his own band.

After the commercial failure of his 1971 concept album Yesterday’s Wine, which RCA didn’t know what to do with, Nelson briefly walked away from music. But being a creator, he instead walked from RCA, refusing to re-up with the label after 15 albums, a run that produced a lot of terrific gems in the individual songs, but never quite the great album he seemed to have in him. 

Nelson had moved to the Austin area by then. Jerry Wexler of Atlantic Records was enough of a fan to not only sign him, but let him record more on his terms. His backing band, the Family, accompanied him on the next album along with Doug Sahm and his band (good company, indeed).

The resulting album, 1973’s Shotgun Willie, was his best to that point and the first from what people think of Willie to this day – with the long hair and beard on the front cover. The originals like the title track, “Sad Songs” and “Devil in a Sleepin’ Bag” fit right in with the Bob Wills and Leon Russell covers.

Willie Nelson Shotgun Willie, Atlantic Records 1973

The following year’s Phases and Stages, a concept record about divorce with the husband and wife’s perspective each getting an album side was another solid effort. It showed that greater creative control suited Nelson. Unfortunately for Atlantic, they decided to fold their country music division that year.

I say “unfortunately” because Nelson, an unplanned free agent, signed with Columbia. His contract gave him full creative control, something he’d enjoyed only tastes of even with Atlantic. And that move would result in a lot of success.

Having veto power over Columbia allowed him to release Red Headed Stranger as he wanted, a spare,

1beautiful album that meshed originals and covers into the story of an outlaw on the run after murdering his wife and her lover. 

Columbia thought the recordings were demos, wondering where the orchestration and heavy overdubs were. He informed them that, no, this was indeed the album.



The label wanted producer Billy Sherrill to take a crack at it. His response? “Did he make this in his living room? It’s a piece of shit! It sounds like he did this for about two bucks. It’s not produced.”

Nelson knew what he had, though. His instincts were on point, as the album was a critical and commercial success, going double platinum and making him a crossover star.

Nelson was one of the outlaw country scene’s biggest successes, along with his friend Waylon Jennings, who’d also chafed at label interference for years. Even with more country chart success, he also didn’t get creative control until the ’70s. As with Nelson, that creative control netted him his greatest critical and commercial successes.

You could pretty much pick up any Nelson studio album the rest of the decade and come home with something quality. He was a country artist, or in the case of 1978’s Stardust, a stellar interpreter of standards, but his talent and aesthetic made him popular with other audiences beyond those who listened to country radio.

When you’re doing at least one album per year, and often more, it can become difficult to keep up quality control. That proved to be the case for Nelson, whose output in the ’80s and ’90s was less consistent. But even then, there’s good stuff to be found: 1985’s Funny How Time Slips Away, 1995’s Spirit and 1998’s Teatro among them.

He also overcame financial troubles caused by mismanagement and poor investments that led to problems with the IRS, even having to release one album whose profits all went to the tax agency.

His artistically improved again, in the latter half of the ’90s. 

Throughout the 2000s, there was gold to be found, particularly in some work that highlighted one of Nelson’s positive attributes. It would be hard to believe that Nelson ever had a report card with “does not work well with others” as a child, given his openness to collaborate with all sorts of artists over the years.

Two Men With The Blues, his 2008 team-up with Wynton Marsalis was a more lively album than one might have expected, a spiritual sequel to Stardust that explores other types of standards (and a couple of Stardust songs).

2003’s Picture in a Frame paired him up with fellow Texan Kimmie Rhodes for a winning duets album. It effectively showcased both, not just for their writing but for their handling of well-chosen covers from the likes of Tom Waits and Rodney Crowell.

Nelson’s creative pursuits turned to occasional acting as well, with 30 films to his credit, starting with a co-starring role in 1979’s Robert Redford/Jane Fonda vehicle The Electric Horseman.


VIDEO: The Electric Horseman trailer 

It’s an easy enough punchline these days to associate Willie Nelson with weed. But while he actively records and performs, Nelson’s not just a consumer of the stuff. He’s actively pushed for legalization for years and is still co-chair of the advisory board of the National Organization for the Reform of Marijuana Laws (NORML). 

He’s advocated for biofuels, with his tour bus having run on them for years, currently on his own brand made from vegetable oils. He was one of the artists to set up Farm Aid. He’s advocated for animal welfare and for LGBTQ rights. At this point, if a right-winger complains about Nelson being “woke”, it would be apparent that person has either been in a cave and/or coma and is thus unaware of who Nelson’s been for decades.

Even as he’s grown older, Nelson does what he does best – create. He’s always adding to a discography full of characters, both virtuous and disreputable, full of humanity and wit.

At this point, Nelson’s voice is more weathered, but still intact. That voice, a baritone that sounded nasal, but wasn’t, always had a lived-in quality, one very well-suited to aging.

As talented as he is as a singer, he also didn’t have to do as others who sang higher like Robert Plant have done in successfully adjusting song range away from the old high notes. But Nelson has clearly adjusted with the smarts of a veteran who knows all the moves, playing with his phrasing and delivery to work around what he can’t do.

Into his ’80s, he continued to make music on his own terms, recording album-length salutes to the likes of Howard and Ray Price and putting out albums where he looks at life and mortality with humor and heart.

Take 2017’s God’s Problem Child, where he worked again with co-writer and producer Buddy Cannon. He originally wanted to call the album I’m Not Dead.

“Still Not Dead” brings the humor (“I woke up still not dead again todayThe internet said I had passed away/If I died I wasn’t dead to stay/And I woke up still not dead again today). So does “I Made a Mistake”, in which he tongue-in-cheek compares himself to Elvis and Jesus.

Reaching a certain age doesn’t just mean seeing your mortality staring back at you in the mirror. It means seeing others in your circle go first, as Nelson warmly sings about on Donnie Fritts’ “Old Timer” and Gary Henderson’s “He Won’t Ever Be Gone”, the latter a tribute to Merle Haggard.

He’s continued in this vein since, aided by an able band that delivers everything smoothly. The core of the family remained steady for decades, with many staying until they couldn’t. His older sister Bobbie, was one such example, playing piano with the band until March, 2021, a year before she passed. Even those who’ve come in as replacements have mostly stayed, ensuring the chemistry holds together. Willie carries the whole affair with an easygoing charm that never slips into coasting.

There’s more humor about mortality (“Halitosis is a word I never could spell/Bad breath is better than no breath at all”) and romantic misadventure (“Well she made my day/But it ruined my life”). There are moments that come across as the chance to learn the Tao of Willie from the feet of the man himself (the beautifully hushed “Energy Follows Thought” off last year’s A Beautiful Time. And there are the smartly chosen covers, as with a version of Charles Aznavour’s “Yesterday When I Was Young” which adds the weight of thousands of miles traveled while sidestepping the middle of the road.

And again, that’s when he’s not doing album-length tributes (two full-length Sinatra cover albums in the last five years, too).

Willie Nelson 90 concert poster at the Hollywood Bowl (Image: Blackbird Presents)

Nelson, as you read this, is on the road. And, yes, I’m aware that sentence now has that song of his in your head.

 He’s got some headlining shows lined up as well as appearances at Outlaw Fest dates throughout the summer. And his annual 4th of July Picnic show will happen again, as it has every year since 1973 (except for 2020 due to COVID).

And as long as he’s able, there’s no reason to think he won’t still be recording. It’s what he does, often very well. His musical legacy was secure long ago. Seriously, he could have retired 25 years ago and enjoyed some well-earned time off. But he’s too busy living, with making and playing music a meaningful part of his life. He clearly knows he still has something to say, so it would be a waste not to say it.

Terms like “national treasure” and “legend” get thrown around a lot, but there’s no question that Willie Nelson fits the bill for both, a man whose talent and continued presence on the scene are gifts worth savoring.

Because, as the man himself sang not long ago, he woke up not dead again today.



Kara Tucker

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Kara Tucker

Kara Tucker, after years of sportswriting, has turned to her first-love—music. She lives in New York City with her partner and their competing record collections.

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